One-pot functionalisation of N-substituted tetrahydroisoquinolines by photooxidation and tunable organometallic trapping of iminium intermediates

Joshua Barham, Matthew P John, John A Murphy

Research output: Contribution to journalArticle

16 Citations (Scopus)
152 Downloads (Pure)

Abstract

Nucleophilic trapping of iminium salts generated via oxidative functionalisation of tertiary amines is well established with stabilised carbon nucleophiles. The few reports of organometallic additions have limited scope of substrate and organometallic nucleophile. We report a novel, one-pot methodology that functionalises N-substituted tetrahydroisoquinolines by visible lightassisted photooxidation, followed by trapping of the resultant iminium ions with organometallic nucleophiles. This affords 1,2-disubstituted tetrahydroisoquinolines in moderate to excellent yields.
Original languageEnglish
Pages (from-to)2981-2988
Number of pages8
JournalBeilstein Journal of Organic Chemistry
Volume10
DOIs
Publication statusPublished - 12 Dec 2014

Keywords

  • iminium salt
  • organometallic
  • oxidative functionalisation
  • photoredox catalysis
  • tetrahydroisoquinoline

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